A Change of Heart

My girlfriend Emily and I have a good sex life, I love her very much; she was the first and only girl I have ever had sex with. She is about 5'6", nice size tits (not too large), long black hair, she's half Phillipino, half English. I'm 6'1", I have long brown hair and a dark goatee beard. We've been going out now for about 3 years, with no serious problems in our relationship, although she works a lot and doesn't stay over as often as I'd like, only twice a week usually.

Emily and I both had the weekend off, which was different for us as she usually worked Saturday morning. It was Friday night, we'd been out to dinner and seen a movie, and had just gotten changed and into bed. Emily put down her book and looked at me.

"Antony," she said.

"Yeah?" I responded.

"When was the last time you dressed up in your 'girlie' underwear?" she had the ghost of a smile on her face.

About 1 year into our relationship I told her that I liked to dress in women's clothes, that I would sneak out at night, stealing bras, panties, stockings off clotheslines around the area, wearing them and ones taken from previous nights. She was a little amused but didn't mind. I can't explain properly why I like to do it. I feel sexy in women's underwear, and the idea of being caught by a woman whilst wearing their underwear thrilled me. It might have something to do with my fear of women; as a kid I was terrified of asking girls out, I couldn't handle the idea of rejection, to the point where I was a 21 year old virgin (before Emily literally seduced me). I began to like the idea that the girls held that power over me. It became one of the things I saw in a sexy girl; she was in complete control regardless of whether she thought she was or not, I would do anything a sexy girl asked.

Her question startled me, as she had never initiated a conversation about it before, nor had she ever referred to it as 'girlie' underwear. I didn't feel I was cheating on her by doing it, but I never talked to her about it, she didn't ask, which was fine with me, due to the embarrassment I felt about it. It was not something she had enjoyed when I tried to take her with me one night. But I didn't ever want to lie to her about anything, especially something sensitive like this.

"Uh... I don't know. A few weeks ago I think." I said, trying to remember.

"You don't know?" She pressed, "You don't remember the last time you put on girlie panties, a bra and a skirt and jacked off, possibly with a dildo up your ass?" She seemed quite calm, yet her explicit choice of words put me on edge.

"Umm... No... Oh wait... I think it was the night after the night we went to that Chinese Restaurant." I said as it came back to me. She considered this for a minute, then put her bookmark in her book and set it aside on the bedside table, before looking back at me again, waiting until she caught me eye.

"So do you have anything new in your ... collection?" she ventured. I did. I had bought a vibrating butt plug since I last dressed in front of her, I don't think she'd ever looked in the drawer and seen it. I'd also bought some balloons at the supermarket a few weeks ago, with the intention of using them as fake tits, by partially filling them with water. I hadn't told Emily what I'd got them for, just said that I wanted them.

"Yeah, I... err... got a butt plug that vibrates.... And I've started using two balloons with a little water in them to simulate boobs...." I hesitantly told her.

"So that's what those balloons were for. I was wondering why you bought them, you wouldn't tell me, now I can see why."

"Yeah, because they're full of water they weigh more and bounce realistically, not like... when I used to stuff the bra with other panties." I explained, trying to draw attention away from the butt plug. In truth she was making me nervous and I was rambling. She seemed satisfied with the explanation.

We sat in silence for a minute or so, my heart pounding wondering why Emily was asking all these questions. Finally she spoke again.

I made to look like I was thinking about it, although I knew right away.

"Well, the bra with the water-balloon tits... the red G-String, the garter belt, stockings... and that sexy little black dress." I listed. She nodded as I said each item.

"And a vibrating butt plug in your ass, of course." She said, smiling at me. I blushed.

"Yeah"

"Okay, that sounds good." She got out of the bed, and started rummaging through her bag.

"Uh... what you looking for?" I tentatively asked.

"I've got this cream for you. It kills hair." She mumbled. I started getting a little worried. Emily had obviously planned something. The fear was good though, it was something that turned me on. I found myself getting hard, with fear and from all the talk about my 'girlie' underwear. I made to ask her what she had planned when she triumphantly brandished it as she found it, and cut me off.

"Get out of the bed, I'm gonna rub this on you." I frowned, and didn't move, started forming a question in my mind, but she went on. "I'm going to rub this on your cock and balls and your ass. Then you're going to have a shower... then I want to have some fun..." She smiled evilly when she said the word 'fun'.

"Em I'm not sure if ..."

"Antony get out of the bed, take off your clothes and let me rub this on you, or you will not get to fuck me at all this weekend. Which would be a shame since I really wanted to try getting fucked up the ass again... but if you're not sure...?" She had a determined look on her face, and I really wanted to try anal sex with her again, so I got out, undressed, and let her rub the cream in.

"See that wasn't hard, although this is!" she giggled as she rubbed some more around the base of my cock. "You know how you always asked me to shave my pussy, but I said I didn't want it itching or getting ingrown hairs; well this way you get to see how itchy it is, and deal with any ingrown hairs. In a few weeks, after your pubes have really started growing back, if you can look me in the eye and tell me it hasn't been uncomfortable, you can shave my cunt yourself." She pressed her lips to my ear as she said the word 'cunt'. She knows I like it when she talks dirty.

"Go have a shower now." She said, returning to normal, "but don't go jacking off, and don't take too long. Make sure you wash it all off."

I went to the bathroom and had a shower. Predictably, all the hair from my cock, balls, and my ass crack fell away as I rinsed. My skin there started feeling supersensitive as I lathered it up with soap, though I was careful not to get carried away and start masturbating. I wanted to fuck Emily so hard now I didn't want to get too excited early.

I got out of the shower, dried off, and went back to the bedroom. Emily was sitting on the bed, laid out were the items I had described to her earlier. She was dressed as a dominatrix.

About 2 years into our relationship we played a game where each of us got to make up a scenario that we would like played out – we'd already done things like sex outdoors in the park at night, the shower, etc. When it was my turn I wrote up a list of things I would like her to do to me as "Mistress Emily". I'd bought a strapon for her, a sexy black latex teddy; a whip, a cane, lubricant, etc. I'd typed up and printed out the list of things I'd wanted her to do; to dress me up in my stolen chick clothes, address me as a bitch or slut, spank me, degrade me, and fuck me with the strapon. I couldn't bear the thought of telling her these things to her face so I wrote them down, sealed them in an envelope, and gave it to her. I left her alone in my room and told her to read it and look in the drawer where all the 'toys' were.

When she came out she was dressed in the costume, and looking very sexy indeed. I'm not going to go into the night in detail, suffice to say she didn't like it very much at all; she lightheartedly spanked me a few times, made me eat her out for a few minutes, and tried using the strapon briefly. She obviously didn't enjoy it, it only lasted a little while before she gave up and we had regular sex. I never asked her to do it again.

And now here she was dressed in the same way, the whip running over her legs, her tits fairly bursting from the tight garment. She had an unreadable expression. She'd obviously had a change of heart, as she sat there looking like a vision of heaven (or hell).

"Let me help you get dressed." She said with a smirk. I waved her to sit back down but she was having none of it. She took my towel, and looked over my naked body, concentrating on my hairless groin. She ran her hand lightly from the tip of my cock down to my balls and back to the top of my ass crack. "Mmmm. Smooth."

Then she started looking over the items on the bed, before selecting the bra and the water balloons. She dressed me like a child, not letting me help, although I could do it all myself and was quite deft and unclasping the bra. Next she fitted the garter belt, and rolled the stockings up my legs, which felt incredible. Then she picked up the G-String, and held it out for me to step into. Once I had both legs in she began to slowly pull it up, but at my knees she stopped.

"I almost forgot. There's something that goes under this." She grinned and picked up the butt plug. Giving it a generous dob of lubricant, she lubed it up, then felt around to my arsehole, sticking a finger in a little with some lube on the tip. I'm ticklish so I shuddered a bit when she did this.

"That good huh, you little slut?" she said, and before I could react she impaled me on the butt plug, causing me to gasp in pain, as she rammed it in hard, in one go. She then yanked up the G-String and let the thin cord at the back run directly over a groove that I had cut into the back of the plug. She gave it a twist, watched me squirm, then picked up the little dress, which was so short on me it was almost like a skirt, and so tight it hugged my form, which is not slight but it accentuated my fake tits. It was a halter top, tied and secured around the back of my neck with a bow. She smoothed it out, noticing that the hem did not quite reach the top of my stockings, making the garter straps visible. She also put my hair in pigtails, then stepped back to admire her handiwork.

"Slut." Was all she said. She had a look of disdain and disgust on her face. She then gathered up all the handcuffs, thumb cuffs and rope from the drawer, and put them in her bag. She also grabbed the blindfold and handed it to me. "Put that on" she ordered.

"Now from now on you are going to do as you're told, without question. You hesitate, I will punish you. Also, your name is 'slut' now and you will answer to it. My name is 'Mistress' and you will address me as such." She cupped her hand over my balls and squeezed for emphasis. "Do you understand, slut?" she said hoarsely in my ear. I swallowed. She seemed to be really enjoying this.

"Yes Mistress." I said.

"Good slut. Now follow me." She led me by hand through the house, as I couldn't see. She then opened the front door, led me out, closed and locked it behind us. I couldn't tell if there was anyone about, but it was about 1am, so I hoped there wasn't. She led me to her car, and opened the door for me. "Get in." she said, and I did.

She drove through a lot of side streets, and when we came to a roundabout, she went round and round and round, until I had no notion of which way we were facing, then she drove off again.

My mind raced as to what she had planned, where we were going. Emily had not liked doing this before, had usually only preferred straight sex or being submissive. She's quite strong willed so I was scared about how far she would go if she started liking being dominant. Finally the car stopped, and she got me out. It was cold. I stood for a few moments, heard a car drive up past us, slowing down as it neared us. It honked its horn as it sped away. I stood terrified, blindfolded. Emily then removed my blindfold; I was standing in front of an Adult bookstore. Emily had her full length leather coat on over her Dom outfit, so she looked normal.

"That strapon you bought for me that other time was a piece of shit." She began. "Here's your credit card. Go in and ask the attendant for the best strapon that they stock, for your girlfriend to fuck you with. Specifically ask for one that will penetrate you deeper and can fuck you harder, as well as be more comfortable for your girlfriend so she can give you the best ass-fuck of your life. Will you remember all of that?" I said I would but she repeated it to me twice more, making me say it back to her. Then she pushed me in the front door, and did not follow.

In the store I immediately noticed the attendant, a young woman, not ugly but certainly not beautiful. She looked over at me and suppressed a laugh. Nervous, I walked up to the counter, he eyes roving over me as I walked up. She tried to keep a straight face as she talked to me.

"Hello, what can I do for you?" she asked. I told her, repeating Emily's words to her. She raised her eyebrows as I said it, blushing feverishly. "I think I can help you with that." She said after a moments thought. She directed me over to the strapon section, and began talking me through several different designs. She giggled as she emphasized how deep each one penetrated, and how hard they were. As she was taking a guy came into the store from the back and looked over at us. The girl waved at him and he walked on, stocking the shelves. I avoided looking at him. She kept talking.

"You see a jelly dong can attach to one of these good models, but a jelly dong wouldn't fuck you as hard as you need, so you could get one of this rubber/jelly hybrid dongs and use that... you can get a vibrating one too." She said, talking directly to me, looking me in the eye and forcefully highlighting the words 'fuck' & 'hard'. I swallowed, nodding to each thing she said. She then waited for me to say something.

"Uh... which one would you recommend?" I stammered.

"For your needs?" She said eagerly. "For you, I would recommend this one," she said, holding one up, "as I think your girlfriend will be able to comfortably wear this, and fuck you good and proper with it. It takes any one of a whole range of dongs, so if she wants she could attach a 12 inch black hard rubber vibrating dong to it and absolutely ream your ass!" She laughed enthusiastically. I swallowed again, humiliated at how she was drawing attention to each point. I heard Emily's car horn outside.

"I'll take it." I said meekly. She then mentioned that it didn't come with any dongs, and recommended a set of 20 dongs of all sizes that fit it, which I got also. As she bagged the items and I turned to go, Emily came in the front door. She looked angry.

"What has been taking so long? What did you get? Did you say what I told you to?" she screeched at me. I reeled under her gaze, mumbled that I had said what she wanted, had just paid, and started opening the bags to show her, when the girl called out to Emily.

"He didn't say anything to me. He's lying to you."

Emily turned and looked at me, fury in her face and eyes. She glared at me for a second, and motioned for me to be quiet when I began to open my mouth. She walked over to the counter. She said to the girl, sweetly:

"Can you tell me exactly what this slut did?" The attendant looked over at me, as I stood terrified, and smiled as she spoke to Emily.

"Sure. He ... It... your 'slut' came in, saw me, and scurried over into the corner there, at looked at the stuff on the wall for about 15 minutes, without saying a word. Then I heard your car horn outside, he grabbed a strapon off the wall, picked up a dong set and rushed over to me, putting it all down with his credit card. He didn't say a word to me, only nodded and signed the slip. Then you came in." She finished. I was mortified. She was lying, but Emily would not believe me – this girl was intentionally getting me into trouble. Emily thought for a moment, then got out her purse, took out a fifty dollar bill, and handed it to the girl.

"Give me that cane there under the counter, the $5 one. Keep the change." The attendant gave her the cane, put the money in the register and took out the change, slipping it into her pocket.

"Thanks. I was only trying to help. I hope I haven't got him in trouble or anything..." She said to Emily, her face all innocence. Emily waved her thanks away, then pointed at me.

"Do you mind if I do this here?" She asked. The girl told her it would be fine. Emily stalked over to me, the cane held firmly in her right hand.

"Put your hands on the counter and bend over, slut." She growled. I bent over, placing my hands on the counter. The girl sat on her stool, smirking at me. She winked at me as Emily pulled up my skirt and bared my ass.

Emily started striking me with the cane. At first I almost jumped, Emily had never hit me that hard before. It hurt. She didn't stop, again and again and again she hit me, on my ass, my upper legs, occasionally hitting my balls, which caused me to yelp in pain, and occasionally she would contact the butt plug, which would send a wave of pain over the entire area.

Tears welled in my eyes, the girl in from of me was smirking at me more now, giggling whenever I yelped or cried out. Just as the first tear left my eye and rolled down my cheek, she shifted off her stool.

"Can I have a go?" she said to Emily. Emily must have nodded because she started moving behind me, then I started getting hit again, but much, much harder this time. When she swung the cane it made a high pitched whine as it approached my cheeks, then a resounding crack as it bit into me. After about 10 of these I was crying freely, whimpering with each stroke. Then she stopped, and I felt her bare hand strike my bare ass. I jumped in pain as my entire ass felt the pain at once. She laughed.

"Hey, I lied before." She said, "Your slut came in and asked for a strapon that could fuck him really hard and deep, so you could give him the best fucking of his life. I lied because I wanted to see you punish him. If you hadn't bought the cane and asked to spank him here, I would have given you the cane and offered to count the strokes for you." She rubbed her hand over my ass, giving it little 'petting' hits, which although light, stung.

Emily didn't seem annoyed.

"Well I was going to spank her anyway, just for being such a slut." She said. The girl smoothed my skirt down and stood me up straight.

"I'm Tammy. I could help you fit this strapon if you like, we've also got a bathroom if you need to give her an enema first, as you don't want this slut's shit on your nice shiny new cock..." she said, also referring to me as 'her'. Emily smiled.

"That sounds really good. I'm Emily. But before I fuck her with this I want to be sure it's the best thing I could use. I want this slut to get fucked so good she will beg me to not stop..." Emily let her voice trail off. Tammy seemed to pick up on what Emily wanted.

"Well I stand by what I recommended. I can give you a demonstration of it if you'd like. I could even do you with it, just to show you how good it can be. I've used this model before, it's the best." Emily seemed really pleased with the idea.

"I'll have to have an enema too then, as I'd like you to fuck my ass with it. I want to try anal sex again tonight, this could be perfect." I could see Emily's hand was under her coat, fingering herself.

They took me out the back of the store; Tammy told the guy (who had been stocking shelves and watching the whole thing) to man the counter, that she'd be back. There was a bathroom where Tammy gave me an enema, a most uncomfortable experience, then after looking at the butt plug I had been wearing threw it in the bin and brought another, larger one which she shoved inside me. She addressed Emily, who was watching closely.